The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

被引：9
|
作者：
Harry, Andy G. [1 ]
Murphy, James [2 ]
Butler, William E. [1 ,2 ]
Tiedt, Rachel [2 ]
Mooney, Aine [1 ,2 ]
Manton, Jennifer C. [1 ]
Pryce, Mary T. [1 ]
O'Donovan, Norma [2 ]
Walsh, Naomi [2 ]
Crown, John [3 ]
Rai, Dilip K. [4 ]
Kenny, Peter T. M. [1 ,2 ]
机构：
[1] Dublin City Univ, Sch Chem Sci, Dublin 9, Ireland
[2] Dublin City Univ, Natl Inst Cellular Biotechnol, Dublin 9, Ireland
[3] St Vincents Univ Hosp, Dept Med Oncol, Dublin 4, Ireland
[4] Teagasc Food Res Ctr, Dept Food Biosci, Dublin 15, Ireland
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2013年 / 734卷
关键词：
Ferrocene; Bioorganometallic chemistry; Dipeptides; Cytotoxicity; Lung cancer; RAY CRYSTAL-STRUCTURE; CANCER CELL-LINES; ANTIPROLIFERATIVE ACTIVITY; BREAST; FERROCENE;
D O I：
10.1016/j.jorganchem.2012.11.041
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
N-{6-(Ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters 2-8 were prepared by coupling 6-(ferrocenyl) ethyny1-2-naphthoic acid 1 to the amino acid ethyl ester GABA(OEt) and the dipeptide ethyl esters GlyGly(OEt), GlyAla(OEt), SarGly(OEt), SarAla(0Et), ProGly(OEt) and ProAla(OEt) using the standard N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of H-1 NMR, C-13 NMR, DEPT-135 and H-1-C-13 COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). Compounds, 2-8 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.2-7.2 mu M. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码：86 / 92
页数：7
相关论文
共 32 条
  • [1] The synthesis, structural characterization and in vitro anti-cancer activity of novel N-(3-ferrocenyl-2-naphthoyl) dipeptide ethyl esters and novel N-(6-ferrocenyl-2-naphthoyl) dipeptide ethyl esters
    Mooney, Aine
    Corry, Alan J.
    O'Sullivan, Dermot
    Rai, Dilip K.
    Kenny, Peter T. M.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (06) : 886 - 894
  • [2] A tandem mass spectrometric investigation of N-(3-ferrocenyl-2-naphthoyl) dipeptide ethyl esters and N-(6-ferrocenyl-2-naphthoyl) dipeptide ethyl esters
    Rai, Dilip K.
    Mooney, Aine
    Kenny, Peter T. M.
    RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2011, 25 (19) : 2905 - 2910
  • [3] The synthesis, structural characterization and biological evaluation of novel N-{para-(ferrocenyl) ethynyl benzoyl} amino acid and dipeptide methyl and ethyl esters as anticancer agents
    Harry, Andy G.
    Murphy, James P.
    O'Donovan, Norma
    Crown, John
    Rai, Dilip K.
    Kenny, Peter T. M.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 846 : 379 - 388
  • [4] The synthesis, structural characterization and in vitro anti-cancer activity of novel 1-alkyl-1′-N-para-(ferrocenyl) benzoyl dipeptide esters
    Harry, Andy G.
    Butler, William E.
    Manton, Jennifer C.
    Pryce, Mary T.
    O'Donovan, Norma
    Crown, John
    Rai, Dilip K.
    Kenny, Peter T. M.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 757 : 28 - 35
  • [5] Synthesis, characterization and in vitro anti-cancer activity of N-(ferrocenyl)benzoyl tri- and tetrapeptide esters
    Corry, Alan J.
    Mooney, Aine
    O'Sullivan, Dermot
    Kenny, Peter T. M.
    INORGANICA CHIMICA ACTA, 2009, 362 (09) : 2957 - 2961
  • [6] Structure-Activity Relationship and Mode of Action of N-(6-Ferrocenyl-2-naphthoyl) Dipeptide Ethyl Esters: Novel Organometallic Anticancer Compounds
    Mooney, Aine
    Tiedt, Rachel
    Maghoub, Thamir
    O'Donovan, Norma
    Crown, John
    White, Blanaid
    Kenny, Peter T. M.
    JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (11) : 5455 - 5466
  • [7] The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl dipeptide esters:: The X-ray crystal structure and in vitro anti-cancer activity of N-{meta-ferrocenyl)benzoyl}-L-alanine-glycine ethyl ester
    Goel, Alok
    Savage, David
    Alley, Steven R.
    Kelly, Paula N.
    O'Sullivan, Dermot
    Mueller-Bunz, Helge
    Kenny, Peter T. M.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (06) : 1292 - 1299
  • [8] N-ortho-Ferrocenyl benzoyl dipeptide esters:: Synthesis, structural characterization and in vitro anti-cancer activity of N-{ortho-(ferrocenyl)benzoyl}-glycine-L-alanine ethyl ester and N-{ortho-(ferrocenyl)benzoyl}-L-alanine-glycine ethyl ester
    Corry, Alan J.
    Goel, Alok
    Alley, Steven R.
    Kelly, Paula N.
    O'Sullivan, Dermot
    Savage, David
    Kenny, Peter T. M.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (06) : 1405 - 1410
  • [9] Synthesis, structural characterization, in vitro anti-proliferative effect and cell cycle analysis of N-(ferrocenyl)benzoyl dipeptide esters
    Corry, Alan J.
    O'Donovan, Norma
    Mooney, Aine
    O'Sullivan, Dermot
    Rai, Dilip K.
    Kenny, Peter T. M.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (06) : 880 - 885
  • [10] The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl amino acid esters
    Savage, D
    Neary, N
    Malone, G
    Alley, SR
    Gallagher, JF
    Kenny, PTM
    INORGANIC CHEMISTRY COMMUNICATIONS, 2005, 8 (05) : 429 - 432
1234